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Convenient synthetic path to ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates and 1-aryl-1,5-dihydro-4H-[1,2,3]triazolo[4,5-d]pyridazin-4-ones

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Chemistry of Heterocyclic Compounds Aims and scope

A convenient method for selective synthesis of ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates and 1-aryl-1,5-dihydro-4H-[1,2,3]-triazolo[4,5-d]pyridazin-4-ones has been developed. New ethyl 1-aryl-5-(diethoxymethyl)-1H-1,2,3-triazole-4-carboxylates were prepared by the reaction of different aryl azides and ethyl 4,4-diethoxy-3-oxobutanoate and readily converted into ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates in high overall yields. Such aldehydes were found to be reactive in several condensation reactions. Reaction of ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates and hydrazine provided 1-aryl-1,5-dihydro-4H-[1,2,3]triazolo[4,5-d]-pyridazin-4-ones in excellent yields.

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The authors are grateful to the Ministry of Education and Science of Ukraine for financial support (project 0116U008067).

The authors thank Dr. Yuriy Slyvka (Department of Inorganic Chemistry, Ivan Franko National University of Lviv) for X-ray crystallographic analysis.

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Authors and Affiliations

  1. Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv, 79005, Ukraine

    Nazariy T. Pokhodylo, Olga Ya. Shyyka & Mykola D. Obushak

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  1. Nazariy T. Pokhodylo
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  2. Olga Ya. Shyyka
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Correspondence to Nazariy T. Pokhodylo.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(8), 773–779

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Pokhodylo, N.T., Shyyka, O.Y. & Obushak, M.D. Convenient synthetic path to ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates and 1-aryl-1,5-dihydro-4H-[1,2,3]triazolo[4,5-d]pyridazin-4-ones. Chem Heterocycl Comp 54, 773–779 (2018). https://doi.org/10.1007/s10593-018-2348-1

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